Methyl chloroformate → HCID 11534069, compound

HRID 644810Notes

Reaction equation

HRID 644810 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH:11]([CH2:12][CH3:13])[CH2:10][CH:9]([NH:14][CH2:15][C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=2)[C:8]2[C:30]([CH3:34])=[N:31][N:32]([CH3:33])[C:7]1=2)=[O:5])[CH3:2].C([O-])([O-])=O.[K+].[K+].C1COCC1.Cl[C:47]([O:49][CH3:50])=[O:48]>O>[CH2:1]([O:3][C:4]([N:6]1[CH:11]([CH2:12][CH3:13])[CH2:10][CH:9]([N:14]([CH2:15][C:16]2[CH:17]=[C:18]([C:26]([F:27])([F:29])[F:28])[CH:19]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:21]=2)[C:47]([O:49][CH3:50])=[O:48])[C:8]2[C:30]([CH3:34])=[N:31][N:32]([CH3:33])[C:7]1=2)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 58662432HCID 58662432, compound

Product 1

HCID 11534069HCID 11534069, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-(3,5-Bis-trifluoromethyl-benzylamino)-6-ethyl-1,3-dimethyl-1,4,5,6-tetrahydro-pyrazolo[3,4-b]pyridine-7-carboxylic acid ethyl ester (0.02 g, 0.04 mmol) obtained in step (vi), and K2CO3 (0.016 g, 0.12 mmol) were charged to a flask under a nitrogen atmosphere. Dry THF (5 mL) was added to this mixture, and the resulting mixture was stirred at room temperature for about 30 min, after which time methyl chloroformate (0.011 g, 0.12 mmol) was added dropwise. The reaction was stirred at room temperature overnight. Water was then added to the reaction mixture and the product was extracted with ethyl acetate. The resulting organic layer was dried over sodium sulphate, filtered, and the filtrate was concentrated under vacuum to provide a residue. This residue was purified by column chromatography over 100-200 mesh silica gel using 8% ethyl acetate in petroleum ether as eluent, to afford the title compound. Yield: 0.01 g (50%).

Workup

  1. stirringThe reaction was stirred at room temperature overnight
  2. extractionthe product was extracted with ethyl acetate
  3. dry with materialThe resulting organic layer was dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under vacuum
  6. customto provide a residue
  7. customThis residue was purified by column chromatography over 100-200 mesh silica gel using 8% ethyl acetate in petroleum ether as eluent

Sources & evidence

ORD record
ord-83a5b81056864c639ab85437492dc3d3
Source dataset
uspto-grants-2010_04
Patent number
US07700774B2

Reaction notes

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